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T. A. SMITKA, R. H. BUNGE, R. J. BLOEM, J. C. FRENCH
1984 Volume 37 Issue 8 Pages
823-828
Published: 1984
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Two new trichothecenes, PD 113, 325 and PD 113, 326, were isolated and their structures were shown to be 12'-hydroxy-2'-(
E)-verrucarin J (
1a) and a stereoisomer of satratoxin H (
3).
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SATOSHI OMURA, MASATSUNE MURATA, HIDEAKI HANAKI, KIYOIZUMI HINOTOZAWA, ...
1984 Volume 37 Issue 8 Pages
829-835
Published: 1984
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Phosalacine, a new herbicidal antibiotic containing phosphinothricin was isolated from the culture filtrate of a soil isolate
Kitasatosporia phosalacinea KA-338. It was a water soluble, amphoteric compound obtained as an amorphous powder (C
14H
28N
3O
6P, MW 365). The antibiotic exhibited antimicrobial activity against Gram-positive and Gram-negative bacteria and some fungi on a minimal medium and the activity was reversed by L-glutamine. It also showed herbicidal activity against alfalfa. It is suggested that phosalacine was decomposed to provide phosphinothricin after its incorporation into microbial or plant cells, and exhibited the antimicrobial and herbicidal activities by inhibiting glutamine synthetase with phosphinothricin although phosalacine itself hardly inhibited the enzyme.
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U. GRÄFE, W. SCHADE, M. ROTH, L. RADICS, M. INCZE, K. UJSZÁ ...
1984 Volume 37 Issue 8 Pages
836-846
Published: 1984
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Griseochelin, C
33H
60O
7, isolated from an asporogenous strain of
Streptomyces griseus represents a novel carboxylic acid antibiotic. The metabolite, which is active against Gram-positive bacteria, forms water-insoluble salts with mono- and divalent cations and binds alkaline-earth metal ions specifically in 2: 1 (x
2M) stoichiometry. Detailed spectral (IR, MS and NMR) studies provide full characterization of its constitution featuring a carboxylic acid function, a substituted tetrahydropyran ring, an allylic OH group which are accomodated within a tetrahydroxylated-octamethyl-C
25 diene backbone.
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KOICHIRO KISHI, KATSUKIYO YAZAWA, KATSUHIRO TAKAHASHI, YUZURU MIKAMI, ...
1984 Volume 37 Issue 8 Pages
847-852
Published: 1984
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In vitro antitumor activities of 13 saframycins, including the potent antitumor component, saframycin A, were determined with the highly sensitive established cell line of L1210 mouse leukemia to investigate structure-activity relationships. Saframycins which lack the α-cyanoamine group or the α-carbinolamine group exhibited much lower cytotoxic activity than saframycin A. The modification of active saframycins either at the C-14 position on the basic skeleton or at the C-25 position on the side chain with bulky substituents resulted in a decrease in cytotoxic activity. These structure-activity relationships corroborated the proposed major mechanism of action for the antitumor activity of saframycin A and supported our proposed model for the saframycin A-DNA adduct.
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A FACILE PROCEDURE FOR THE PREPARATION OF DOXORUBICIN ANALOGS
DEREK HORTON, WALDEMAR PRIEBE, OSCAR VARELA
1984 Volume 37 Issue 8 Pages
853-858
Published: 1984
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Two successful routes have been developed for preparation of 3'-deamino-3'-hydroxydoxorubicin (11), based on protection of the 14-hydroxyl group of the aglycon by using
tert-butylchlorodimethylsilane. The key intermediate, 14-
O-tert-butyldimethylsilyl-7-
O-(3, 4-di-
Oacetyl-2, 6-dideoxy-α-L-
lyxo-hexopyranosyl)adriamycinone (9), was successively deacetylated and desilylated in high yield to give the desired product 11. This route constitutes a general method of access to glycon-modified doxorubicin analogs. Compound 11 showed high antitumor activity
in vivo in the murine P388 lymphocytic leukemia assay.
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ENZYMATIC CLEAVAGE OF C-N LINKAGE IN VALIDOXYLAMINE A
NAOKI ASANO, MASAYOSHI TAKEUCHI, KOTARO NINOMIYA, YUKIHIKO KAMEDA, KAT ...
1984 Volume 37 Issue 8 Pages
859-867
Published: 1984
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The enzymatic cleavage of C-N linkage in the degradation of validamycin A by
Flawbacterium saccharophilum was examined using
N-p-nitrophenyl derivatives of validamine and valienamine as synthetic model substrates for validoxylamine A. Incubation of
N-p-nitrophenylvalidamine with the membrane fraction from the organism led to formation of
N-p-nitrophenyl-3-ketovalidamine, and succeeding cleavage of C-N linkage. As the products of the cleavage step, one was identified as
p-nitroaniline and another keto compound could not be purified enough because of its instability. However, on the basis of its hydrogenation products, the structure of the keto compound could be established as 5D-(5/6)-5-
C-(hydroxymethyl)-2, 6-dihydroxy-2-cyclohexen-1-one. The same experiment was carried out with
N-p-nitrophenylvalienamine. In this case,
N-p-nitrophenyl-3-ketovalienamine could be isolated as an intermediate but the desired keto compound from the cleavage step could not be isolated because of its instability. The participation of two enzymes, that is, a dehydrogenase and a C-N lyase on the cleavage of C-N linkage was assured, and moreover, the analysis of its products, together with those of the previous studies allow us to propose a degradation pathway of validamycin A by
Flavobacteriwn saccharophilum.
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YOSHIO TAKEDA, VIVIEN MAK, CHID-CHIN CHANG, CHING-JER CHANG, HEINZ G. ...
1984 Volume 37 Issue 8 Pages
868-875
Published: 1984
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The antibiotic ketomycin is formed from shikimic acid
via chorismic acid and prephenic acid. Phenylalanine and 2', 5'-dihydrophenylalanine are not intermediates in the biosynthesis. Degradation of ketomycin derived from [1, 6-
14Clshikimic acid showed that prephenic acid is converted into ketomycin with stereospecific discrimination between the two enantiotopic edges of the ring, the
pro-S-R edge giving rise to the C-2', C-3' side of the cyclohexene ring of ketomycin.
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T. CIFTCI, T. A. BORKMAN, L. E. MCDANIEL, C. P. SCHAFFNER
1984 Volume 37 Issue 8 Pages
876-884
Published: 1984
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A study of nine hexaene antibiotics resulted in their assignment to three subgroups on the basis of their bioactivities. Separation of individual components of the nine antibiotic complexes was accomplished by thin-layer chromatography. Similarities and differences among members of the subgroups were established by thin-layer chromatography, spectrophotometry and high performance liquid chromatography. Two antibiotics (endomycin and hexafungin) were found to be similar.
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ROBERT C. MEARMAN, CHRISTOPHER E. NEWALL, ALAN P. TONGE
1984 Volume 37 Issue 8 Pages
885-891
Published: 1984
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The synthesis of a series of analogues of clavulanic acid, possessing a substituted 1, 2, 3-triazole ring in place of the exocyclic hydroxyl group, is described. Quantitative structureactivity relationships in this series are discussed.
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I. IN VITRO ACTIVITY
M. LIMBERT, N. KLESEL, K. SEEGER, G. SEIBERT, I. WINKLER, E. SCHRINNER
1984 Volume 37 Issue 8 Pages
892-900
Published: 1984
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Cefodizime possesses a broad antibacterial spectrum including staphylococci, streptococci and
Enterobacteriaceae. Neisseria gonorrhoeae and
Haemophilus influenzae are also highly susceptible to cefodizime. Because of its β-lactamase stability cefodizime is active against bacterial strains producing especially plasmid-coded enzymes. The MICs of cefodizime are slightly higher than those of cefotaxime, but with most Gram-negative bacteria they are lower than those of cefazolin, cefotiam and piperacillin. The
in vitro activity of cefodizime is not dependent on inoculum size, or on the pH and composition of the test medium. Cefodizime did not induce
in vitro resistance of
Staphylococcus aureus or
Escherichia coli. Because of its binding properties to PBPs 1A/B and 3, cefodizime leads to filamentation of Gram-negative rods and, at only slightly higher concentrations, to bacteriolysis.
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II. COMPARATIVE STUDIES ON THE PHARMACOKINETIC BEHAVIOR IN LABORATORY ANIMALS
N. KLESEL, M. LIMBERT, K. SEEGER, G. SEIBERT, I. WINKLER, E. SCHRINNER
1984 Volume 37 Issue 8 Pages
901-909
Published: 1984
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The pharmacokinetic properties of cefodizime, a new aminothiazolyliminomethoxycephalosporin, were studied in laboratory animals and compared with the pharmacokinetics of another long-acting cephalosporin, ceftriaxone. Both cephalosporin derivatives showed high affinity (33-99%) for serum proteins. High and prolonged blood respectively serum levels of the antibiotics were achieved following subcutaneous and intravenous injection into mice, rats, rabbits, dogs and monkeys. Cefodizime elimination half-lives ranged from 1.17 hours in mice to 3.53 hours in rabbits compared to ceftriaxone half-lives ranging from 0.73 hour in mice to 7.31 hours in rabbits. The antibiotics were well distributed in the body and penetrated into tissues and body fluids to a high degree. Particularly high and prolonged levels were detected in the lungs, liver and kidneys of the experimental animals. Large amounts, approximately 35-55% of the given dose, were recovered in the urine of rabbits and dogs, while the recovery rate in the bile of rabbits was only 0.57% for cefodizime and 1.08% for ceftriaxone.
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JUN MATSUMOTO, KUNIHIKO SAITO
1984 Volume 37 Issue 8 Pages
910-916
Published: 1984
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In relation to a previous paper (J. Antibiotics 32: 734- 739, 1979), the effect of some antibiotics on endogenous phospholipid degradation of rat liver was investigated by slice and perfusion techniques. Polymyxin B inhibited this degradation most strongly, benzylpenicillin, chloramphenicol and peplomycin inhibited moderately, and carbenicillin, cephaloridine and streptomycin did not inhibit. Tetracaine and ethylenediaminetetraacetic acid, which are not antibiotics, also showed inhibitory effects. The results strongly suggest that besides their usual antibiotic actions, some antibiotics may participate in endogenous phospholipid metabolism and biomembrane functions of host cells.
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ANN H. HUNT, GARY G. MARCONI, THOMAS K. ELZEY, MARVIN M. HOEHN
1984 Volume 37 Issue 8 Pages
917-919
Published: 1984
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AKIHIRO YOSHIMOTO, YASUE MATSUZAWA, TOMOYUKI ISHIKURA, TSUTOMU SAWA, T ...
1984 Volume 37 Issue 8 Pages
920-922
Published: 1984
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THE EFFECTS OF VALINE, ISOLEUCINE, ISOBUTYRIC ACID AND 2-METHYLBUTYRIC ACID
V. P. MARSHALL, J. I. CIALDELLA, J. A. FOX, A. L. LABORDE
1984 Volume 37 Issue 8 Pages
923-925
Published: 1984
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MIKIKO ITO-KAGAWA, YASUO KOYAMA
1984 Volume 37 Issue 8 Pages
926-928
Published: 1984
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ANTIBIOTIC HR 810 WITH GENTAMICIN AND AMIKACIN AGAINST MULTIRESISTANT PATHOGENS
GERHARD SEIBERT, MICHAEL LIMBERT, NORBERT KLESEL
1984 Volume 37 Issue 8 Pages
929-930
Published: 1984
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TATSUO ITO, KAZUNORI OHBA, MASAO KOYAMA, MASAJI SEZAKI, HIROYOSHI TOHY ...
1984 Volume 37 Issue 8 Pages
931-934
Published: 1984
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AKIHIRO YOSHIMOTO, OSAMU JOHDO, YUKIO TAKATSUKI, TOMOYUKI ISHIKURA, TS ...
1984 Volume 37 Issue 8 Pages
935-938
Published: 1984
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SATOSHI OMURA, KIYOIZUMI HINOTOZAWA, NOBUTAKA IMAMURA, MASATSUNE MURAT ...
1984 Volume 37 Issue 8 Pages
939-940
Published: 1984
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I. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 2'-DEOXYOXANOSINE
KUNIKI KATO, NAOMASA YAGISAWA, NOBUYOSHI SHIMADA, MASA HAMADA, TOMOHIS ...
1984 Volume 37 Issue 8 Pages
941-942
Published: 1984
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